


Oscar's First Train Ride

by Damien_Kova



Category: RWBY
Genre: M/M
Language: English
Status: Completed
Published: 2017-04-25
Updated: 2017-04-25
Packaged: 2018-10-23 23:16:00
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,194
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10729308
Author URL: https://archiveofourown.org/users/Damien_Kova/pseuds/Damien_Kova
Summary: Oscar takes his first train ride while Ozpin tries his best to recover. While Ozpin is away, Oscar finds his train ride to take an enjoyable turn.





	Oscar's First Train Ride

Today was the day of Oscar the farmhand’s first train ride. He was on his way to Mistral just as Ozpin convinced him to do. Unfortunately, he would be alone on this ride.“Oscar, I’m telling you, you’ll be fine on this train. The only people on board are you, the conductor, and those three travelers that have no aura. I sense no ill intent from them either.” Ozpin did his best to comfort Oscar. His own aura was nearly tapped out and he needed to rest on his own, partially disconnecting from Oscar to regain some more of his own aura instead of leeching off Oscar’s. “Now, if you’ll excuse me, I need to rest and regain my own aura before I accidentally take too much of yours. Neither of us would want that to happen, would we?”  
  
“Well…of course not!” Oscar tried arguing. He knew Ozpin was right, but he just didn’t want to be alone. “I’m just nervous. How long will you be gone? This is my first time out of my home, because of you by the way, and you just want to leave me?” He made his way through the cars on the train until he got to one he felt was quiet enough for him. “Fine… Just don’t take forever. We are going to see your friends afterall.”  
  
“Yes, yes, I know. And I’m sorry for taking you from your home but we need to do this. I won’t be long. Five hours tops.” Ozpin’s voice rang through his head again.  
  
“Five hours?!” OScar nearly shouted as he took hold of the handle that hung above his head. “…Fine! Just, are you sure that these guys on the train have no ill intent towards me? I can’t exactly fight, even with you in my head.”  
  
“For the last time, Oscar. I’m sure. Now, I’m leaving because I’m running on empty.” His voice faded away in an echo as Oscar sighed to himself.  
  
The farm boy was now alone in the train car. He had a solid three hours before the train met his destination in Mistral. As the train began to move, he thought he heard the sound of glass shattering. Out of fear, he refused to move from his place. Please let that have just been my imagination… He thought to himself. After a few moments, he felt two small feminine hands touch his plump ass. As a farm hand, all the food he had eaten was home grown either on his family’s farm or nearby locals. Exercising and home grown food sent any possible fat he could’ve had straight to his ass. It wasn’t too large compared to his body but it was just more than enough to be considered a bubble butt.  
  
Out of nowhere, those two hands began squeezing and groping his soft jiggly cheeks. Running her slender fingers into one of his belt loops, she yanked the back of his pants down from around his rear, exposing the few freckles on each cheek and his tight asshole. A soft gasp left his lips as the cool air of the train A/C on his ass.  
  
He had had enough at this point and decided to turn around and see who was behind him. It was a woman! _Who is this?!_ He thought as he saw her multicolored eyes swap as she blinked and smiled at him. He watched as she adjusted the brown portion of her hair to cover her face before waving to him and taking a soft bite on his right cheek. The bite caused him to gasp once again, covering his mouth with his free hand in fear of being heard.  
  
Seeing his reaction, Neo smiled and bit his plump rear another time, sliding her tongue around the marks she was leaving behind on it. She watched him force his eyes forward away from her. Spreading his cheeks, she squeezed them again just like before, watching as the excess skin pushed between her fingers just a bit. After another moment of playing with said soft cheeks, she dove in, sliding her tongue into his tight little hole before he could get a word in to try and tell her to stop.   
  
He couldn’t describe how the feeling her tongue inside of him made him feel. It wasn’t bad and it wasn’t amazing. It was more of just a nice feeling to have something wet exploring his insides. Much to his bewilderment, he could feel his pants tightening around his crotch. As he felt her begin to motorboat his ass, he could feel his pants grow even tighter and feeling like they were about to pop right off of his body. They stayed this tight as she pulled her face away from between his cheeks and slipped a finger into his hole. Due to her saliva, Neo’s finger didn’t bother Oscar as it slid inside of him. She slid her finger in and out of his hole slowly at first, but curling it to try and stretch him out just a bit.  
  
Just at this very moment, as if timed perfectly, the three men Oscar passed on his way to his car while talking to Ozpin approached the two of them with smirks on all of their faces. “Mind if we join you two? It’s very clear your little boy-toy is enjoying you toying with his ass. Maybe we could toy with it as well~?”  
  
The small criminal smirked and nipped Oscar’s ass once more, as if trying to silently saying he was hers to use. After that she smiled and took a few steps away from the boy, gesturing to him. As she did so, she slipped his pants off of him to leave his lower body exposed to the three strangers and herself. Surprisingly, he wasn’t wearing any underwear so his cock flew free and stood at his natural eight inches.  
  
“My my!~ Look at that!” The hairiest of the three men started, sitting in front of Oscar, the boy reaching for his boxers. “I was right. He was really enjoying having his ass played with.”  
  
The smallest of the group snatched his pants and smiled even wider. “You can have these back, boy! IF you do something for each of us!”  
  
“My name is Oscar! And what do I need to do to get those back?” He tried to sound angry, but his voice came out a bit seductive instead for a reason he had no clue of.  
  
“I want a handjob.” The hairy one spoke up from behind Oscar.  
  
“I want a blowjob.” Said the one holding his pants.  
  
Oscar glared over to the other one. “And what do you want?”  
  
“Not sure, yet. I’ll figure it out.” He shrugged and pushed Oscar onto the floor in front of his friend that wanted a handjob.  
  
“Just so you know, I’ve never done anything like this before.” He wanted to get his pants back before the train ride was over and he had no idea how long it would be until it was over. He had to hurry.  
  
Neo stood beside Oscar and pulled off the stranger’s pants, silently gasping as his eleven inch cock rested against his own thigh. She took a gentle hold of Oscar’s hand, kissing his cheek softly before wrapping Oscar’s fingers around the man’s cock.“That’s the way, boy. Just hold and stroke it. My name is Frost.” He watched as Oscar took his time working over his cock. “The one who wants a blowjob is Dill. The other one is Damian.”  
  
Oscar simply nodded as Neo helped him move his hand faster and faster along the man’s cock. Once it started to grow hard in their hand, Neo helped the farm boy twist his hand to try and add more pleasure to Frost. Without having Neo help him, Oscar moved his other hand and used it to hold the man’s balls in his hand. He played with them in his palm like he was trying his best to massage them.  
  
Frost ran his hand through Oscar’s hair and bucked his hips lightly into the boy’s hands. “That’s the way, boy! For someone who’s never done this, you know just what to do!” As Oscar stroked faster and faster, Frost could feel himself starting to throb and pulse inside of the boy’s hands. After a few moments, Frost took a firm hold on Oscar’s head and moaned. Neo saw this action and took a step back as rope after rope of cum stained Oscar’s cheeks and one or two even coating his right eye.  
  
The young boy gasped as cum coated his face. Shivering as Neo licked the cum from his eye and swallowed it, he felt her quickly push him towards the other guy. Before he could talk, he felt Dill pull him towards his cock. That feeling from earlier was back. Having a cock pressed to his lips made him feel a mixed sense of unknown pleasure and partial shame from being used like this. Looking over to his side, he opened his mouth before Neo quickly ripped his shirt off and hid it behind her. She wagged her finger as if saying he can’t get it dirty. He didn’t even pay attention to her as he slipped his lips around the twitching shaft. He sucked around the head as he felt Dill’s hands tighten their hold in his hair. His eyes widened as he felt himself be pulled down to the base of Dill’s lengthy member, the tip touching the back of Oscar’s throat but not enticing his gag reflex. Oscar placed his hand onto the man’s inner thighs before pushing himself off just a bit, sucking the entire time. Once he was at the top, he slipped himself off with a wet and satisfying pop.  
  
“Don’t forget to swirl your tongue, kid. Just sucking on it won’t be enough to make me cum. I mean, you want to get your pants back, right?~” Dill smirked and pulled Oscar back to his cock.  
  
Silent, Oscar opened his mouth and started licking along the sides of the member in front of his face. Up from the bottom of the shaft to the head and swirling his tongue around the head before kissing it and engulfing it again to the back of his throat. The boy had learned to breath through his nose rather early, so he had no problem staying down as long as he needed. He transitioned from sucking as hard as he could to swirling his tongue around the meaty shaft inside of his mouth. As he began bobbing his head, he could feel something start to press against his rear.  
  
It felt wet, slick and warm. Another moment passed before he quickly learned it was one of Neo’s slender fingers entering his ass. He paused for a moment, wondering why he didn’t feel pain and why the pleasure he felt grew stronger. He did his best to put the thought out of his mind as he went back to dutily sucking the cock that rested on his tongue. Once more, he began swirling his tongue and bobbing his head to try and give the guy more pleasure. The only thought in his mind being to make these men and this woman happy with him so he could get his clothes back and leave.  
  
He could feel the finger inside of him move itself in and out at a steady pace as Neo’s other hand reached around and took a light hold of his cock. He was now bobbing his head as fast as he could, suckling the cock and doing his best to ease Dill over the edge. After a few moments, he could feel the hand wrapped around his member tighten its grip around the base of his shaft. Her fingers were blocking something from escaping his body. The growing pent up pleasure had nowhere to go as he felt rope after rope of a hot sticky liquid hit the back of his throat and stick to it.  
  
He did his best to swallow it down as Neo sat him in Damian’s lap. “I’m the last one for you to please. Now I’m going to let you choose what to do to-” Before he could finish his sentence, he felt Oscar began grinding his hips into the man’s crotch. Having a plump, soft rear grind against his dick sent chills up Damian’s spine. The older man didn’t care anymore, he lifted Oscar up just enough to pull out his now erect cock and force the boy back down in one swift motion.  
  
Oscar tried to shout in pain but a pleasured moan left his lips instead as he felt the hot meat fill his body. Neo wrapped her hand around Oscar’s member one more time to stop his orgasm from erupting as the man under him found a rhythm both men enjoyed. The farm boy could feel himself squeezing and clenching his anal walls around Damian’s member as the man kept pushing in and out of his body like a piston. After a few more thrusts, Oscar began moaning in the same rhythm that was being used to plow him.  
  
Dill decided it was time to get up and go check how long until they reached their stop, leaving Neo with the three men now. The ice cream themed girl nudged the man using Oscar’s ass like a toy to get his attention. She smiled and made a fist, unclenching it to suggest cumming inside of him because time was running out.  
  
Damian realized she was right and pushed Oscar onto his back and onto the floor so the farm boy’s green eyes looked into Damian’s own blue eyes. The older man could see just how much Oscar was enjoying this by the moans leaving his lips and the look in his eyes begging to be used more and more. Even if he would never say it, his body was reacting to the pounding he was receiving and it was loving it! The view was quickly blocked by Neo’s petite body thought as she dropped her panties and plopped herself onto Oscar’s face. The young boy didn’t know what to do but decided to lick around and suckle on her clit as he was pounded into until the session would stop. The older man smiled and gave a few more powerful thrusts before groaning happily and filling Oscar’s ass with near scalding ropes of cum. As he filled the boy, he watched pure delight fill Oscar’s eyes as his orgasm was once again denied by Neo yet he had pleased the people he needed to to get his clothes back.  
  
After a moment, Damian pulled himself out of Oscar’s hole and sat back in the seat he was in. ”Damn, that was a heavenly ass! I want more of it!~”   
  
Frost couldn’t help but chuckle from hearing his friend adore the ass of this young boy the three of them just used as a fuck toy. He smiled and leaned down beside Oscar as an idea formed in his head. “Hey, boy. I got an idea for you!” He smirked over to Neo and back to Oscar. “We have a bit more time before our train ride ends, how about you fuck both me and Damian one more time and we’ll all let you go. At least us guys. I have no idea what this little lady has in store for you.” The very thought of being used by two men at once sent Oscar over his very pent up limit. Silently, he came all over his chest, nearly coating it in his own semen. “Well, I’ll take that as a yes then.” Frost smiled, pulling Oscar into his lap and quickly onto his own cock. All while Damian forced his own member into Oscar’s mouth before the boy could even moan properly.  
  
Both men stood to their feet and held Oscar between them, holes locked and clenching around their members. He was so small compared to them that he just sat there in the air, his arms and legs dangling down but not touching the floor. Oscar began instinctively swirling his tongue around the man in his mouth while Frost started thrusting into him from behind. Neither one of the older men really cared for the fact they were using someone underage for their own pleasure. The boy agreed to it, even if he was in a cum drunk state.  
  
The two began thrusting into Oscar’s limply hanging form in opposite rhythms so neither one of them left the boy’s willing body. Everyone was extremely sensitive from the past short while on the train ride and the boy’s amazing body that they enjoyed toying with. Neo, however, was a bit disappointed that Oscar hadn’t made her climax while she was sitting on his face, but this train ride wasn’t about her. She smiled to herself and took a seat a few steps away from the spitroast scene in front of her. The sight was incredible for her to watch. Two large men pumping their meat over and over in rhythm into a young boy’s eagerly awaiting body. She could see Oscar’s eyes shine in pleasure as he let the men use him like a toy.  
Everyone’s mind was starting to turn to mush from the pleasure they were all getting, self-caused or otherwise. The men inside of Oscar began pumping themselves in and out at a much faster rate as the farm boy’s body began clenching tighter than a few moments ago on each cock. He was far too lost in lust to think about sucking on the man’s member but his warm, wet mouth was enough for Damian to be happy with the hole he was fucking.  
  
After about ten more minutes of mindless fucking and masturbating, all four people in the car climaxed together. Oscar coated the floor in his cum while he felt rope after rope of sticky cum fill his ass and his throat. He couldn’t take the pleasure anymore and blacked out from the mind-numbing pleasure. The last thing he could hear were the two men laughing and leaving the train car they were in and the clicking of heels moving closer to him.  
  
The next thing he knew, he was on a hotel bed, cum leaking from his ass and still on his stomach as if he was carried on his back and no one cleaned him. Checking the time, he remembered Ozpin would be back any moment, so he rushed to the bathroom and got in the shower. While he was washing himself off and all the cum was no longer visible on his body, he heard a clear clicking sound in his head, as if something connected.  
  
“Oh! I see you made it to the hotel in one piece just like I said. How was your first train ride, Oscar?” Ozpin asked, happy to have returned to his new home.  
  
“It was great! I can’t wait for the next one! Never would’ve thought it’d be so fun!”


End file.
